Hydrochloric Acid → 1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522536Notes

Reaction equation

HRID 1522536 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1.Cl>>[CH:12]([N:8]1[C:6]2[N:7]=[CH:2][CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]=2[C:10]([CH3:11])=[N:9]1)([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 866776236-chloro-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 895439301-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Procedure

The title compound was prepared in the same manner as described for example 139 (step a) from 10% Pd/C(degussa) (0.457 g, 0.215 mmol), and 6-chloro-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1.09 g, 4.30 mmol) wherein the stir time was 4 h Upon acidification to pH 3 with 1M HCl, the contents were extracted with EtOAc (2×) and the combined organic layers dried over MgSO4, filtered, and concentrated in vacuo. The collected solid was dried in a vacuum oven at 45° C. for 3 h. The final product was collected as 0.826 g (84%). 1H NMR (400 MHz, DMSO-d6) d ppm 1.48 (d, J=6.57 Hz, 6 H), 2.63 (s, 3 H), 5.21 (quin, J=6.69 Hz, 1 H), 7.52 (d, J=4.55 Hz, 1 H), 8.63 (d, J=4.55 Hz, 1 H), 13.77 (br. s., 1 H). LCMS(ES) [M+H]+ 220.2

Workup

  1. extractionthe contents were extracted with EtOAc (2×)
  2. dry with materialthe combined organic layers dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe collected solid was dried in a vacuum oven at 45° C. for 3 h
  6. customThe final product was collected as 0.826 g (84%)

Sources & evidence

ORD record
ord-56397c61d1fb4e3d9730039f9cf22482
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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